tert-Butanol → Tert-butyl 4-(bromomethyl)benzoate

HRID 1647055

Reaktionsgleichung

Reaktionsgleichung von HRID 1647055
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:12][CH:11]=1.C(O)(C)(C)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 6386tert-ButanolHCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimide2×HCID 116297491,1-Dimethylethyl 4-methylbenzoate

Produkt 1

HCID 11414578Tert-butyl 4-(bromomethyl)benzoateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (NBS) (35.8 g, 0.20 mol) was added in several portions to a solution of 1,1-dimethylethyl 4-methylbenzoate (prepared by the reaction of the respective acid chloride with t-butanol.) (38.0 g, 0.20 mol) and benzoyl peroxide (0.36 g, 1.5 mmol) in carbon tetrachloride (1200 mL) at vigorous reflux. Another portion of benzoyl peroxide (0.36 g, 1.5 mmol) was added just before the final addition of NBS. After the foaming subsided, the reaction mixture was cooled to room temperature, washed with water (2×60 mL) and dried over magnesium sulfate. Filtration and concentration provided an oil that was purified by HPLC on silica gel eluting with a mixture of hexanes and ethyl acetate to give 1,1-dimethylethyl 4-bromomethylbenzoate (21.4 g) in 40% yield.

Aufarbeitung

  1. washwashed with water (2×60 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration
  4. customprovided an oil that
  5. customwas purified by HPLC on silica gel eluting with a mixture of hexanes and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ba818f1a44eb47469763929fed7d9a57
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05182263

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